For wind turbine applications, there is a cyclic load-varying process between rolling elements and raceways in pitch bearings. This kind of motion can also lead to radial fretting. However, this is seldom addressed under grease-lubricated conditions in the literature. In this study, grease-lubricated point contact problems have been investigated experimentally under cyclic load-varying conditions. The findings revealed that as the load-varying range diminishes, the variation in grease film distribution becomes more subtle and the rate of discharge of thickener fiber clusters in the stick zone decelerates. This is due to the fact that the rate of change in the Hertz contact radius is reduced and the migration of grease is weakened during the unloading process. Due to the large apparent viscosity of grease with a high soap content, entrapped grease is not easily discharged during loading, and the thickness of the film in the stick zone progressively increases as the soap content of the grease is augmented. This also causes the variable load zone to wear out more easily. As the grease is subjected to repeated loading and unloading, there is a gradual reduction in film thickness, and larger thickener fiber clusters tear, resulting in a flattened form and shear thinning. Grease containing sulphur–phosphorus additives demonstrates a superior effect on reducing fretting wear within the large variable load range but generally proves effective for smaller load-varying ranges. This study may offer insights into the degradation of grease under variable load motion and methods to prevent radial fretting wear.